Photo Credit: Jewish Press

Dear Dating Coach,

A guy was recently suggested for me and he sounds great except for the fact that he is five years younger than me. I know logically that I would definitely be ok if he was five years older than me, but I can’t seem to wrap my head around being the older one. Five years older! He is aware of my age and apparently does not mind at all, but I am hesitant to say yes to the shadchan. What do you think?


Not Ageless


Dear Ageless,

This is a public services announcement to all you Lego failures like me. My oldest loved Lego and could spend hours (days!) putting together those tiny pieces to create complicated masterpieces. For those that are unfamiliar, Lego sets come with these Great American Novels camouflaged as picture books that are meant to guide you through your Lego creation. Page after endless page of hieroglyphics created for mini-mechanical engineers that encourage you to locate the tiny red piece. (No, the other tiny red piece!) I valiantly tried and spectacularly failed to live by the book of Lego law, while my toddler-turned-developer seamlessly built mini-villages and hamlets to market to the Lego masses. But here’s my little secret, just between you and me, of course. If at the end of your build, you find yourself stuck with one oblong green piece, don’t despair. No need to turn back to page 481, section H, column 9, row 17 to figure out where you might have gone wrong. Just throw out the green piece. Your Lego design will still look flawless, and I won’t tell. Promise.


Age is just…

It is always a nice feeling when someone who sounds so promising is suggested to you. You were likely initially excited to hear the many positives about this potential match but were unprepared for the age difference. You admit that your feelings were colored by your own preconceptions and that you would not balk in the same way if he was the one who is five years older. Feminism, uneven expectations, and societal pressure aside, the world at large is often more comfortable with the man being older than the woman. We get you.


A Number…

Yet you’ve been presented with a potential match, one that you agree sounds great. While we all have our own hope for the future and often share a universal vision of the ideal “catch,” we also know that life is not about crossed t’s, and checked boxes. At this stage of the dating process, you have learned that being the “right age” does not guarantee a “right match.” You know that our mindset and our willingness to adjust allows us to often accept a gift we have overlooked before. You have not heard that he is unkind, lazy, or spiteful. His only flaw, youth. Perhaps, it’s best to replay the wonderful qualities you have heard about him in your mind. Remind yourself that the shadchan feels very positive about your potential connection. Think that over and allow yourself to revel in the possibility.

Now, make him older than you.

Would you say “yes?” If so, then say “yes.” Worst case scenario, you go out, and he is as childlike as you fear, and you don’t go out with him again. Best case, you’ve met your perfect match.


And Mine Is Unlisted.

Sure, we hope that all of the pieces we have constructed through the years in our heads align as we date. But in the end, your masterpiece is the only thing that matters. If one piece didn’t make the cut, move on. You’ll be the one with the beautiful creation, and no one will ever think about that green oblong piece, because you didn’t need it to create a lasting design.


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Henni Halberstam is a Dating and Marriage Coach whose expert advice will help you navigate dating and relationships in order to ensure a successful marriage. You can contact her at to schedule a phone session.